A great article by Nicholas Reynolds in the journal Studies in Intelligence looks at Ernest Hemingway's surprisngly extensive dabblings in spy work during World War II, which included connections with the State Department, OSS, FBI, and the Soviet NKVD. Not surprisingly, Papa relished the danger and excitement of intelligence work but wasn't actually very good at it. Here's his best, and most Hemminwayesque, scheme from his time in Cuba:

While other American sailors were volunteering their boats and their time along the East Coast to spot U-boats, Hemingway’s concept of operations went further. He would pretend to be fishing, wait until a German submarine came alon side to buy fresh fish and water and then attack the enemy with bazookas, machine guns, and hand grenades. Hemingway would use Basque jai alai players to lob the grenades down the open hatches of the unsuspecting U-boat.

Hemingway had a good ON contact, the redoubtable Marine Col. John A. Thomason, who was the writer’s kind of man: veteran of World War I infantry combat, a distinguished short-story writer and sketch artist, a heavy drinker, and an intelligence officer. Thomasontold Hemingway that he and his crew would stand no chance of success against the highly trained submariners of the Third Reich, but the Marine could not say no to Hemingway, especially since the author had the support of the ambassador.

In the end, the ONI arranged for Hemingway to receive just enough gear—guns, ammunition, grenades, a direction finder, and a radio—to make the mission viable. The ONI even threw in an experienced Marine to sail with Hemingway. It would all be highly secret. Hemingway clearly relished the secrecy and the danger. He especially enjoyed developing his cover, which was that he was performing oceanographic research for the Amerian Museum of Natural History. The Pilar’s war cruises lasted from the second half of 1942 through most of 1943. Although Hemingway patrolled diligently for much of the time, he only spotted one German submarine, which sailed away on the surface as he approached.15

After traveling to Europe as a war correspondent, he did eventually spend a few days gathering intel with an underground French maquis group -- an operation that was undoubtedly brave, if not particularly productive.

Though Hemingway was publicly anti-Communist, he maintained contact with the NKVD from as early as 1935, and it was his Soviet contacts that allowed the author to enter Spain for the research that eventually became For Whom the Bell Tolls. However, according to declassified Soviet records, his handlers became frustrated that he failed to produce any useful polticial intel for them. Ultimately, Moscow found just as useless an asset as Washington.

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